(E)-1-ethoxydimethylsilyl-2-phenylethene | 135351-09-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-1-ethoxydimethylsilyl-2-phenylethene
• 英文别名: ethoxy-dimethyl-[(E)-2-phenylethenyl]silane
• CAS: 135351-09-6
• 化学式: C₁₂H₁₈OSi
• 分子量: 206.36
• InChiKey: YNHJEHFGVIVIDT-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  二甲基乙氧基硅烷 、 苯乙炔 在 platinum(II) chloride 2-dicyclohexyl-phosphino-2',4',6'-triisopropylbiphenyl 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以64%的产率得到(E)-1-ethoxydimethylsilyl-2-phenylethene
  参考文献：
  名称：

  Xphos ligand and platinum catalysts: A versatile catalyst for the synthesis of functionalized β-(E)-vinylsilanes from terminal alkynes

  摘要：

  Hydrosilylation of functionalized terminal arylalkynes with a variety of silanes catalyzed by PtCl(2) or PtO(2) in the presence of the air-stable and bulky Xphos ligand was investigated. Regardless of the electronic nature ( electron withdrawing or donating group) and the position (o, m, p) of the substituents on the aromatic ring, a single beta-(E)-styrylsilanes was obtained in good to excellent yields. The regioselectivity of the H-Si bond addition was found to be governed by steric effects induced by the bulky Xphos ligand. A dramatic regioselectivity was also observed when functionalized terminal aliphatic alkynes were employed as a substrate and in these cases regioisomeric beta-(E)-vinylsilanes were generated with excellent selectivity. (c) 2008 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2008.05.028

文献信息

• Preparation of Vinyl Silyl Ethers and Disiloxanes via the Silyl-Heck Reaction of Silyl Ditriflates
  作者：Sara E. S. Martin、Donald A. Watson

  DOI：10.1021/ja407748z

  日期：2013.9.11

  Vinyl silyl ethers and disiloxanes can now be prepared from aryl-substituted alkenes and related substrates using a silyl-Heck reaction. The reaction employs a commercially available catalyst system and mild conditions. This work represents a highly practical means of accessing diverse classes of vinyl silyl ether substrates in an efficient and direct manner with complete regiomeric and geometric selectivity

  现在可以使用甲硅烷基-Heck 反应从芳基取代的烯烃和相关底物制备乙烯基甲硅烷基醚和二硅氧烷。该反应采用市售的催化剂体系和温和的条件。这项工作代表了一种非常实用的方法，可以以有效和直接的方式获得不同类别的乙烯基甲硅烷基醚底物，并具有完全的区域异构和几何选择性。
• RhCl(PPh₃)₃/NaI Catalyst System for Hydrosilylation of 1-Alkynes: Stereodivergent Syntheses of E- and Z-Alkenylsilanes with Heteroatom Substituents on Silicon
  作者：Atsunori Mori、Eisuke Takahisa、Hiroshi Kajiro、Kazunori Hirabayashi、Yasushi Nishihara、Tamejiro Hiyama

  DOI：10.1246/cl.1998.443

  日期：1998.5

  Both (E)- and (Z)-alkenylsilanes are synthesized by the reaction of hydrosilanes and 1-alkynes catalyzed by RhCl(PPh3)3/NaI or RhI(PPh3)3 highly selectively.

  (E)-和(Z)-烯基硅烷均可通过在RhCl(PPh3)3/NaI或RhI(PPh3)3催化下，高度选择性地由氢硅烷与1-炔烃反应合成。
• Ruthenium-catalysed disproportionation between vinylsilanes and mono-substituted alkenes via silyl group transfer
  作者：Yasuo Wakatsuki、Hiroshi Yamazaki、Masato Nakano、Yasuhiro Yamamoto

  DOI：10.1039/c39910000703

  日期：——

  Selective cross-disproportion between vinylsilanes and various mono-substituted alkenes is catalysed by [RuCl(CO)H(PPh3)3]1; the mechanism of this reaction has been elucidated based on reactions of 1 with vinylsilanes as well as those of the resulting ruthenium–silyl complex with alkenes.

  选择性交叉不均匀反应发生在乙烯基硅烷和各种单取代烯烃之间，催化剂为[RuCl(CO)H(PPh3)3]1；该反应的机制已经基于1与乙烯基硅烷的反应以及得到的钌-硅烷复合物与烯烃的反应进行了阐明。
• Dehydrogenative silylation of terminal alkynes by iridium catalyst
  作者：Rie Shimizu、Takamasa Fuchikami

  DOI：10.1016/s0040-4039(99)02174-7

  日期：2000.2

  Dehydrogenative silylation of terminal alkynes with hydrosilanes proceeds in the presence of iridium catalyst to afford the corresponding silylacetylenes. When phenylacetylene and triethylsilane were heated in dry DME in the presence of Ir4(CO)12–PPh3, (2-phenylethynyl)triethylsilane was obtained in 96% yield with little of hydrosilylated products. The present method is applicable for a variety of

  末端炔烃与氢硅烷的脱氢甲硅烷基化反应在铱催化剂的存在下进行，得到相应的甲硅烷基乙炔。在Ir 4（CO）12 -PPh 3的存在下，在干燥的DME中加热苯基乙炔和三乙基硅烷时，得到的（2-苯基乙炔基）三乙基硅烷收率为96％，几乎没有氢化硅烷化产物。本方法适用于各种末端炔烃和氢硅烷，以高收率和高选择性得到相应的甲硅烷基乙炔。
• Norbornadiene as an Efficient Hydrogen Scavenger for the Palladium-Catalyzed Conversion of Hydrosilanes to Alkoxysilanes
  作者：Sundarraj Sudhakar、Tien-Yau Luh

  DOI：10.1021/jo025886z

  日期：2002.9.1

  A palladium-catalyzed mild and efficient method for the alcoholysis of hydrosilanes containing a C=C bond in the presence of norbornadiene (NBD) is reported. The highly strained NBD acts as a hydrogen scavenger, which abstracts the hydrogen produced during the process, protecting the C=C bond from being hydrogenated.